Methyl chloroformate → HCID 17930266, compound

HRID 840071Notes

Reaction equation

HRID 840071 reaction equation
C(C[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH2:13][CH:12]=1)(O)=O.[CH2:14](N(CC)CC)C.[CH3:21][O:22][C:23](Cl)=[O:24]>CCOCC>[CH2:21]([O:22][C:23](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH2:13][CH:12]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 22621662HCID 22621662, compound

Product 1

HCID 17930266HCID 17930266, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 220 mg (1.3 mmol) of 1-(7-carboxyheptyl)-cyclopropene in ether was cooled to 0° C. Triethylamine (0.20 g, 2 mmol) was added, then 0.12 g (1.3 mmol) of methylchloroformate was added. After 2 hours at 0° C., the reaction mixture was transferred to a separatory funnel. The ether phase was washed with water (2×) and brine, dried over magnesium sulfate, filtered and stripped. The product was dissolved in ethanol, cooled in an ice bath and treated with 1 ml of a 21% sodium ethoxide in ethanol solution. The reaction mixture was stirred ½ hour, then water and ether were added. The ether phase was washed with 1N sodium hydroxide solution, water, and brine, dried over magnesium sulfate, filtered and stripped to give 10 mg of 75% pure 7-cycloprop-1-enyl-heptanoic acid ethyl ester.

Workup

  1. customthe reaction mixture was transferred to a separatory funnel
  2. washThe ether phase was washed with water (2×) and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. dissolutionThe product was dissolved in ethanol
  6. temperaturecooled in an ice bath
  7. additiontreated with 1 ml of a 21% sodium ethoxide in ethanol solution
  8. additionwater and ether were added
  9. washThe ether phase was washed with 1N sodium hydroxide solution, water, and brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-24265f7a01684d4f9e9637b952e3ce85
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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